Provocateur Turned Self-Saboteur: Why Kanye West's Support of Trump Is His Biggest Misstep

Kanye West’s endorsement of Donald Trump is officially the lowest moment of his career.

The beginning of this baffling saga forever resides in the part of the brain where traumatic memories are buried: a bleached blond Kanye, not quite looking his self after a stint in the hospital for what we now know was an opioid addiction (reportedly fueled by sleep deprivation and the 10-year anniversary of his mother’s death), meeting with the then-President-Elect, who he would’ve voted for had he voted at all, at the Trump Hotel in December 2016. They posed for photos, discussed social issues in private and exchanged an awkward handshake that serves as a metaphor for just how fucking weird their friendship is.

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For the more forgiving fans out there, that wound had healed by the time Kanye returned to Twitter last week and announced a new album, along with a full-length collaboration with Kid Cudi (Kids See Ghost) and fully-produced albums for Nas, Pusha T and Teyana Taylor, all of which are scheduled to be released in the next few months.

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Days later, though, Kanye decided to reopen that very wound by reigniting his peculiar relationship with the far-right. First, by voicing his support for Candace Owens, a black conservative pundit who once called Black Lives Matter protestors “a bunch of whiny toddlers, pretending to be oppressed for attention.” Then, by sharing a vlog from Scott Adams, creator of Dilbert and disciple of The Donald. And, inevitably, by reiterating his love for the Salmon-colored Sith Lord himself.

Watching him meet with Donald Trump was one thing (who knows, maybe some good could've come from it), but seeing Kanye West sport a MAGA cap—to dumb racists as the white hood was/is to the KKK—feels like witnessing the beloved Dropout Bear morph into George Condo’s dark, twisted caricature in real time. It’s troubling. It’s baffling. It’s betrayal. Sure, Trump and Kanye share similar megalomaniac traits. But how do you reconcile watching the guy who heroically called out a sitting President for not caring about black people cozy up to the current sitting President who cares even less about black people (and seemingly everyone who isn’t a straight, white, American male)?

Jesus didn’t walk for this shit.

I’m not the only one who feels betrayed. For the first time, the usual adoration Kanye West receives from fans, critics and fellow artists alike has been replaced with concern, confusion and contempt—and they’re not afraid to show it. J. Cole (who has already reassessed his idolatry of Yeezus) rolled his eyes. Frank Ocean came out of hiding just to shake his head. John Legend tried his best to enlighten his good friend on his worrying ways. Questlove, the eternal hip-hop elder, is stunned. Someone even Michael Jordan Crying Face’d The College Dropout, a day I never thought I’d live to see. Lord knows what Jay makes of all this.

In fact, the only positive reaction to Kanye’s pro-Trump tweets—aside from close confidantes like Kim Kardashian, Chance The Rapper and CyHi The Prynce (who, to quote William Ketchum, has spent the last few days riding in the Bronco with Ye)—has come from right-wing leeches like Bill O’Reilly, Paul Joseph Watson and Alex Jones, who hilariously invited Kanye onto his Infowars broadcast to fight the “thought police” and “control-freak vampires.” Something in the matrix has gone horribly wrong when racists are defending Kanye West against you.

Is this really the first time that Kanye’s status as a cult hero—at least among his very large and loyal fan base—is under legitimate threat?

The last time Kanye forced us to ask this type of question was nine years ago when he famously interrupted Taylor Swift's victory speech at the 2009 MTV VMAs. But this is different. This is worse. At least with the VMAs you didn't have to squint too hard to see a trusted truth-teller, loaded off a cocktail of Hennessy and grief, calling bullshit on an awards show for overlooking black excellence—the greatest performer of her generation, at that—in favor of lily-white mediocrity while bravely sacrificing himself in the process.

As the media, the general public and even the president pulled out their pitchforks, we stood by Ye because, yes, he was—and still is—a phenomenal artist, and also because he was right. In his support for Trump, however, it’s difficult to see the moral game plan, and it’s forcing even the most ardent of Kanye fans to waver. If the VMAs built a case for Kanye West vs. Taylor Swift and the general public, this Trump saga is turning it into Kanye West vs. The People. His own people.

Right now, the provocateur is looking more like a self-saboteur.

Kanye’s endorsement of Trump—and right-wing pundits like Candace Owens—also carries more dangerous implications than any controversy he’s been embroiled in before. In what little explanation he’s given so far (which is irresponsible in itself), Kanye claims he's trying to free people from their “mental prisons,” to encourage us to “move in love,” which suggests some sort of spiritual awakening, a father-of-three trying to make this divided, volatile world a better place for his kids. (A cynical eye might see a future presidential candidate trying to curry favor with voters who wouldn’t otherwise vote for him.)

Kanye’s heart could well be in the right place, but his calls for love, peace, and unity only serve to benefit one side. Not the side who are suffering from the consequences of the policies and ideologies that are seeping from the White House like a gas leak. But the side who are currently using Kanye as a propaganda tool, touting his misguided tweets as red-pill proof that Donald Trump is making Black America Great.

Kanye siding with Trump isn’t a meeting at the halfway point; it’s the Speaker of the House abandoning his party and crossing the aisle, receiving a MAGA cap upon entry like an NBA rookie on draft night. This ain't Michael Jackson meeting Reagan. The lines in the sand—markers for where Trump’s wall will be built—are too deep for Kanye just to kick it with the enemy and think everything’s still cool. Maybe it's our fault for not replacing Kanye as Speaker of the House earlier. Or assuming he was in our party in the first place.

What Kanye is doing is foolish and, should he continue down this murky path, he'll have more to contend with than just losing a few fans (I wonder if the MAGA crowd will fill any empty seats). But I refuse to believe Kanye's this naïve. He knows this. People close to him are telling him as much. We’re told he’s in good shape mentally, that this is still the same old Ye from the telethon and the VMAs. Well, here's the thing: it is.

From bringing pink Polos to Roc-A-Fella to marrying the Queen of reality TV and incorporating the Confederate Flag in his Yeezus merch (a harbinger of what was to come), Kanye West has always sought to move the needle, redefine culture, and make history with broad, bombastic strokes. Supporting Trump is just his latest—albeit shakiest—attempt to prove he’s still Provocateur Number One. And when you consider he has five albums to promote, which is how I always imagined Kanye West would bow out, his behavior begins to feel like an aging star launching a Hail Mary in what could well be his final game. Not because the clock's winding down, but because the game's not over.

Now that his legacy—in both music and fashion—is cemented, Kanye is testing to see if it breaks. How far are we willing to follow him before we abandon him? How much further can he push the needle before it snaps? How “free” is Kanye West if he can’t do whatever the hell he wants, fans and friends be damned?

Music has always been the antidote to Kanye’s antics. Despite everything, there’s no reason to start doubting the man’s musical prowess now. I just hope that when the dust settles on this cruel summer, we can look back and say it was all worth it—for us and for Kanye West.